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The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.
Welcome back to their episode
of the Startup Therapy Podcast.
This is Ryan Rutan, joined
As always by Will Schroeder,
my friend, the founder,
and CEO of startups.com.
Will, it's no secret at this
point anybody that listens
that you and I spend most of
our days talking to startup
founders about businesses, new
and old, you know, gone and,
and imagined and yet to be.
How often is it that the very
first idea that we come up
with the very first plan is
the one that's gonna get us all
the way to the promised land?
Damn near never.
Ah,
never surprised
me.
Right.
We wanna have the
fantasy of it, right?
Yeah.
The fantasy is this, like
when people say like, Hey, you
know, you started a successful
business, you know, how did
you come up with the idea?
And I always tell the, the, the
same thing I said, I didn't,
I. Like, oh, would you mean
somebody else came up with that?
I was like, no, the idea for
this business didn't exist.
So I came up with a dumb one.
Yeah, yeah.
That, that got us here.
Yeah.
Um, and I always use that as
a way to explain that, that
the businesses we're supposed
to build are an evolution.
Learning about what's
supposed to be built.
Yes.
Like it would sound awesome
if it was just like,
Hey, here's exactly what
I'm supposed to build.
Yeah.
And I'll just go do that.
It reminds me of like, if
someone was just starting off in
their life and you're like, Hey,
I'm not gonna make any mistakes.
I'm just gonna start with
exactly what I'm supposed
to do for every decision.
Yeah.
And.
Execute perfectly.
Right.
And by the way, you're about
five years old at that point.
Right?
So you've got all the
life experience you need.
Exactly.
You know everything
that's coming.
Yeah.
It's funny that, but but
it, it is sort of par
for the course, right?
Yeah.
This is most of
the conversations.
We end up having founders
believe some version of that.
Here's what I think the
problem is, you know, kind
of what we'll unpack today.
I think because we get so sold
on this idea that the product
has to be exactly this way.
Yeah.
Yeah.
We prevent ourselves from
keeping our minds open saying.
Does it?
Or like, are we actually
holding the startup back?
Yeah.
Because we're
unwilling to let it
evolve.
Oh, that's an interesting
way of looking at this.
Yeah.
Yeah, yeah.
So to what extent are we
not, not just that we're not
moving it forward as fast as
it could be, but that we're
actually holding it back.
Okay.
I like that.
I like that.
Here's a dumb example
'cause it's probably not
even true, but I just, but
I, I wanna point it out.
When Uber started, if you
recall, way back in the
day, Uber started as a,
a way to basically make.
Black cars, right?
Like private black cars like
Lincoln Town Cars accessible.
It wasn't intended to overturn
the taxi industry at the time.
It was very hyper specific.
It was everyone's
private driver.
That was the initial tagline.
That was the tagline
That's right of of Uber.
Right?
And so in that initial.
Reckoning if you were, uh,
Travis and Garrett from
Uber, the, the, the founders,
and you were thinking to
yourself, okay, this is it.
We're gonna be all about
getting all these black
cars that are typically Unad
addressable and you like,
it's very hard to get them,
hard to find, hard to book.
Yep.
Tons of downtime, and we're
gonna give you essentially
a quasi taxi, but a limo to
get where you want to go.
And we were like, no,
that's the business.
It's not another business.
Think of what was lost,
what would've been lost if
they stuck to that model.
Dude, I would've walked so
many more places in life.
If Uber hadn't existed
as it does now, it
would've been awful.
There's a million cases
and, and I bet a lot of the
folks listening, they're
a case of this right now.
Yeah.
Where they're saying
to themselves, but this
model's not working.
This model has to work.
And it's like maybe, or maybe
the model that's supposed to
work, lo and behold, isn't about
giving people access to limos.
Like, like maybe there's a
different version that would be
a hundred times more valuable
if we just let it evolve.
And I think we have a hard
time letting it evolve because
of, you know, this kind of
myth of the perfect plan.
You know what I mean?
Yeah,
for
sure.
And, and I think that's,
that's where it starts.
It's like we, we spend so
much time thinking about it
that of course we must have
thought everything that we
need to at this point, now
we're gonna start building it.
So we've made some plans
and I think you're, you're
right, like part of that
challenge then that perfect
planning that we've done.
Actually starts to blind
us to, to real feedback.
Like, and it's so funny
sometimes man, like I'll, I'll
talk to founders like my getting
customers, um, sessions that
I do on Mondays and Fridays,
we run into this all the
time where they're like, and
they're just not getting it.
And I'm like, okay,
what are they getting?
What are they taking
away from this?
What are they telling you?
They're telling me this
and this and this and this.
And I'm like, okay.
Have you, if that's what they're
telling you over and over again,
are you starting to internalize
any of that feedback?
Like or are you just
saying No, they're wrong?
Yeah, like, because here's
the deal, they still have
the credit cards that they
need to vote with to prove
that you're right and they're
current, consistently voting no.
So let's go with maybe
there's some validity to that.
And, and it's just tough.
And I get it.
Like, you know, after you put
so much time into it, there's
the whole sunk cost fallacy.
There's the, I don't want
my baby to be ugly thing.
I've already told everybody
this is what I'm building.
How could I possibly
build anything else?
But man, the, I cannot overstate
the necessity of like that early
and continuous user validation.
Let give you an example.
The most common scenario that
I hear, and I'm sure there's
folks listening that, that
have been through this, the
most common scenario I see is.
But I just raised
money with this idea.
There's nothing
more humiliating.
Okay.
And I'm just gonna call
because I've been there.
Then saying to investors,
this is the future.
Going and proving that this
is the future, only to find
out it's not the future.
Right.
In fact, you were way
off and having to go back
and say, just kidding.
Now this is the future.
That's hard to do.
It is.
It's hard to do, but
it's important because
what's the alternative?
If you've realized that's not
the future, you're building
towards a future that you
already know doesn't exist, at
some point are the investors
gonna be happy that you go
back to them and tell them, I
was super wrong and I already
have your money, so I'm gonna
go try to be more right now.
Right?
Not exactly the kind of
thing that inspires a vote
of confidence at a lot of
levels, but on the other
hand, like that is what gives
them a chance at, at getting
a return on their money.
So it look, they may
not be happy to hear it.
But they're gonna be happier
than you just plowing
forth into something you
know is not gonna work.
This took me a long time to
internalize, because early
in my career, whenever I was
making any kind of decision
for the company Yeah.
And, and I was communicating
that to my staff and I had
to change my mind later,
it made me feel weak.
Yeah.
It made me feel like, uh, as
a weak leader, which to be
fair, I was like 22, 23, 24.
So were you.
So that's kind of what
we were a work leader.
We were weak leaders.
Right.
Like that was, that
was just an accurate
assessment of the situation.
I felt, rightfully so, that
I had to overcompensate for
my clear lack of experience.
Right.
Especially, again, back then,
different era where like young
CEOs didn't exist and so you
were a sideshow at best to
begin with and you, you were
exactly what people expected to
fail, like for all the reasons.
Okay.
It was really hard for me
back then to be able to say,
Hey, that was a mistake.
Let's move left instead
of right, kind of thing.
Because at the time I was
so preoccupied with me being
wrong that I wasn't willing
to let the product or the
organization be right.
I got a piece of feedback early
on that was so beautiful and I,
I probably didn't appreciate it
for what it was in the moment.
Early, early, early.
I, I wanna say, I don't
remember what they were calling
him at the time, but early,
uh, it was a, an uncle of
a, a close friend of mine in
university early at Salesforce,
like really early, like
chief revenue officer before
that's what they called it.
Something like that.
Right?
Just somebody came in, I
was trying to explain to
me and he was debating
back with me and, and you
know, he was significantly
more experienced and just
super, super smart dude.
He said he is like, look.
I'm hearing what you're saying,
but at this point it feels like
you're trying harder to be right
than to find out what is right.
I love that.
I love that.
Right.
And I was
like, in the moment I was like,
Ooh, that stings once the sting
wore off probably years later.
I mean, it's something I
still hear that at times now.
Yeah.
When I find myself pushing
back against something, I can
hear his voice saying, are
you trying harder to be right?
Or find out what's
actually right?
I'm like, dammit, I
think I'm doing it again.
And what's interesting to
me about that is it's, it's
all tied back to our ego.
Yeah, right.
A hundred percent.
We have this sense back when
I was making those moves early
in my career and, and I had
to make a change of sorts.
My issue, I would say was
like 80% my own ego, like
how it affected me in 20%.
My concern as to how it
might've affected the
business, I don't know that
I could have changed that.
I mean, part of that was
just my own evolution.
I, yeah, I think it is
because in the beginning,
a pivot feels like a
confession of failure right?
To ourselves, to anybody
around us, and I think
that that can't be ignored.
I think what you eventually
realize after you've
gone through enough of
them is that it's not a
confession of failure.
It's, it's a calibration towards
what might actually work better.
And once you realize
that you become a bit
more comfortable again.
There's still times where
like that's uncomfortable.
Particularly if you've just
been out, like shouting to
the rooftops on LinkedIn
or you've raised phones.
The articles have been
written about it, right?
Like you've gotten some
publicity and now you're
going, well shit, that's
not exactly what we're
gonna go do now, but, right.
We had this happen with a, a
company we did called Afford
It, and it was essentially
what Affirm is today.
Oh yeah.
Um, buy now, pay pay
later years before Affirm.
And, uh, we got
into the business.
And it was going great.
Like we were selling tons of
products, but then there's
the part where, where you
have to pay later, which
means we have to collect.
And any kind of credit
business isn't a credit
or banking business.
It's a collections business.
Yes, a collections business.
It's all what it comes down to.
It's not hard to get
people to take free
money, to get cool stuff.
A hundred percent right.
Like, like any loan is about
collection, not disbursement.
Anyway, we got into the
collections part of it, and
all of a sudden we're on
the phone collecting from.
Single moms who were using
this to, and, and this wasn't
like a story, this just kept
happening, that were using this
as a way to like buy an Xbox
for their kid for Christmas.
I grew up with a single
mom and so like I knew
this process really well.
Yeah.
And the last thing
that I wanted to do was
collect from single moms.
Right?
Hey, you're behind
on your payments.
Oh, what?
Oh, oh really?
I'm, yeah.
Nevermind.
Bye.
Just kidding.
Right.
And so, so, okay, so,
so here's the thing.
We had raised a bunch of
money from really prominent
investors on a very big
concept that was working.
That's the worst part.
That was working.
And we had a bunch
of term sheets for a
Series A at the time.
At the time, I'm like.
Oh shit, how do I
get out of this?
Like, I don't wanna
be in this bit.
I don't want to.
I don't wanna
do this anymore.
I was like, now to be fair, that
decision got made for us because
we were headed right into the
financial crisis, like 2007 era.
Yeah.
Everything dried
up over overnight.
And like we couldn't
raise any more money.
Wasn't
that, wasn't a whole lot
of money being tossed at
subprime lending at that.
No.
There, there were, unless
you were the governments
of Iceland, really?
Ireland and Cyprus, who were
like, it was not real possible.
We'd love to buy some
de class repackaged
debt.
That'd be great.
Right, right, right, right.
And so anyway, none of
it was, I wasn't willing
to let go even though I
didn't even wanna do it.
Like that's the worst part.
I didn't even wanna do
that business anymore.
I just raised a bunch of money.
I'd just gotten to LA at the
time and I was everywhere at
all the events and everything.
Talking about this business.
I put my entire
ego into it, right?
Yeah.
My reputation and everything
into this business, and
overnight I was like, I
just made a giant mistake.
I wasn't willing to let
it go because of my ego.
Yeah.
I, I think that's it.
It comes down to like, if,
if I'm thinking of it from a
spectrum perspective now, and
it's got, you got ego on one
end and you've got, I'm gonna
call it agility on the other.
The closer we can get away
from, you know, the further
we can get from, from ego
and get closer to agility, I
think we're, we're better off.
But it's hard, right?
It is a struggle to let go.
And I think to your point, it's
really hard to do that until
we've sort of gotten punched in
the face by, by getting it wrong
with ego and maybe accidentally
gotten some wins from agility
and your case, like you were
forced outta the business.
And, and look, you don't
need to spend a long
time answering this, but.
What do you think would
have happened had we not
run into the, the, the whole
financial crisis, right?
Like had more capital have
been available now, you
were already kind of like, I
don't wanna do this anymore.
What's the crystal ball?
Like the, what
would've happened?
Would you have continued
with the business?
Yeah.
Wouldn't it become a firm?
I
mean, no.
I, I would've, I wouldn't have
become a firm and again, I,
when, when people are like, oh,
I had this idea before that,
I did this idea before that.
Sure.
That was the easy part.
What Max Lein did, you
know, with Affirm was a
hundred x what I would've
ever done with afford it.
Uhhuh.
I mean, to, to be fair,
that's like me saying, well,
I had a pretty good game
and so I guess I'm Tom Brady
right in, in this equation.
He's Tom Brady.
I'm some idiot that plays
flag football with a
bunch of 50 year olds.
Right?
Like not to same athlete.
Yeah.
So my point is Affirm
would've been just fine.
Who knows what would've
happened to us.
But I can tell you, and, and
I'm, I don't like to admit
this, I don't like to admit
the fact that I would have
pressed forward and did.
Not because I thought it was
the right thing for me, the
market, the world, et cetera.
Yeah.
But because my ego was so
attached to it, because I
had so many people that I
had committed to that I,
I wasn't willing to stop.
And it, running out of money
was kind of the only way that
was gonna get me out of that.
And, and even
then, I spent like.
18 months, 24 months nonstop,
banging my head against the
wall to try to like, get capital
before we eventually gave up.
So I didn't go out easy either.
Like it was guns blazing.
That's, I mean, that's the
paradox, man, of, of building
products versus building
your identity into it.
That's a big part of this.
At that
point where we're so wrapped up
in it, it's like we, we can no
longer isolate ourselves from it
makes it really hard to let go
because we're essentially saying
I'm killing off a part of myself
in order to kill this thing off.
That's a hard
decision to get to.
You know, something that's
really funny about everything
we talk about here is
that none of it is new.
Everything you're dealing
with right now has been done a
thousand times before you, which
means the answer already exists.
You may just not know
it, but that's okay.
That's kind of what
we're here to do.
We talk about this stuff on
the show, but we actually
solve these problems all
dayLong@groups.startups.com.
So if.
Any of this sounds familiar.
Stop guessing about what to do.
Let us just give you the answers
to the test and be done with it.
Let's stick with this.
This goes back to the dream.
The dream is, hey everybody,
this was the original idea.
This was the original plan.
This was the reason you quit
your last job and joined to
work for equity or whatever.
You know, it's the reason
investors put money in.
It's really hard to say
that that plan didn't work
and expect the same level
of enthusiasm for new plan.
It's so much easier to
say It's tough, man.
Let's just stick with old plan
because it was the oldie timey
original and force that through.
It takes balls to be
able to say I was wrong.
Okay, let's full
stop right there.
I was wrong and that's okay.
I wasn't willing to do it.
I am now, but at the
time I was not for sure.
It's,
yeah,
and man, and again, like
in hindsight, way easier to
see, but like clinging to
that original version isn't
loyalty, it's not toughness,
it's not strength of character,
it's potential self-sabotage.
Right.
But being able to see that
in that moment, it's up
there amongst, I think, the
hardest of the challenges
that we face as founders.
Particularly 'cause it often
comes at such an early stage.
Yeah.
That we have so little else
to go on other than our own
enthusiasm, our own ideas, our
own thoughts, and a little bit
of feedback from the market.
And then that little bit of
feedback from the market is
going counter to what we hoped
it's brutality at its finest.
Well, okay, so
let's build on that.
I wanna talk a little
bit about why I don't
have the same issue now.
Where was my evolution so
that I could get to the point.
Sure.
And hopefully other founders
listening can kind of get to
that, that same, uh, point.
This came from a few
different places.
One, it came from once I started
to understand that clinging to
the original idea, just 'cause
it was the original idea mm-hmm.
Was just dumb.
Like it wasn't, I couldn't come
up with a good reason all other
than it sounded cool that it
was actually the best, most
strategic, most mature way.
Again, in most cases, I
was attaching it to ego.
Now when I tell people
about this ego, et cetera,
invariably I'll hear a lot
of people say, yeah, well I
don't have the same ego to it.
First off, bullshit.
Okay, second off, second off in.
Is that your
ego talking?
Yeah.
This kind of is, but okay,
so, but here's what's changed.
Fast forward years later.
And we start fundable.com, which
would later become startups.com.
Now, by this point, I had seen
in a bunch of my own businesses,
things just evolve, right?
Yeah.
Things just go a different
direction and that be better.
So we launched fundable.com.
It's a crowdfunding platform.
This is like 20 11, 20 12.
It turns out.
It was just a bad idea.
And, and Ryan, obviously I'm
not saying this to you 'cause
you were there, you know
exactly what I'm talking about.
A bad idea being, it just
wasn't like that viable
equity crowdfunding would
not go on to be as an entire
market.
Correct.
Wasn't, wasn't, wasn't
what everybody thought
it was gonna be.
But even,
especially back then.
So with that said, because
I had the benefit of seeing
what happens when I don't
evolve that time, me and
certainly you and the rest
of the team were very open.
To trying something else.
That's essentially what led us
to startups.com, which is, you
know, much different, much, much
better, more viable business
that is about to celebrate.
Its start of its 14th year.
Right?
Wild.
Absolutely wild.
Two deals from now, I think.
Yeah, right.
Exactly.
But stick with that for
a sec. Had we been like,
no equity crowdfunding.
You know, once you start,
start a plan, you don't change
it and you see it through, we
would've gone outta business.
Yeah.
We're like, come hell or high
water, we would be sitting in
high water and hell right now,
like 30 other companies who
who tried the same thing did.
And the only difference
between us and them was our
willingness to be able to say,
what if it's something else?
What if the answer is elsewhere?
Go back in time.
'cause for me, there
were a couple of specific
things that happened.
I think that that
helped me with this.
One of them was, a few
situations started to
appear partially just from
experience, partially just
from time in the game where the
adaptation became proactive.
The evolution was
proactive, not reactive.
I think part of it was early on
I was being told I was wrong.
I was, whether it was the
market investors, people around
me, whatever it was, I was
being told, you are wrong.
So the evolution was
basically somebody else
telling me I needed to evolve
or something else telling
me I needed to evolve.
I think as I grew and as I
built more and more, what I
started to see was, there's
actually some signals of
this from the market, right?
Things like going out and
doing customer interviews
before you start building shit.
Really talking to the people
that you're building for
making sure that you filter
this down to a really like,
not just ideal client profile,
but like early adopter.
The people who are really gonna
go after this thing at an early
stage, knowing that we'll move
beyond that, but to gather
that feedback and so that the
pivot would become sooner.
Before I had decided and done
so much and become kind of
fixed in my thinking one, but
also because it felt proactive.
I had gone out and discovered
reasons why maybe I needed
to evolve as opposed to being
smashed in the face with a
sign that says Evolve or die.
And I'm like, well,
then I quit on dying.
Well, let's talk about that.
Let's talk about like
what letting it evolve.
Actually looks like, you
know, what does that mean?
At the, the very least, it's
about giving up some control
over what you believe the
idea absolutely has to be.
Right?
It's, it's about stepping back
and saying, look, I think if
we really wanna see this thing
survive and thrive, yeah.
We have to let it grow
into what it wants to be.
Now.
Now sometimes what it wants
to be doesn't look like
what we wanted to build.
Of course, man.
Like your first plan is,
is, is a guess at best.
Right.
Only the market can
confirm or deny that guess.
Like we can't sit around
and think through it
and be like, okay, yes.
Now we're right.
Will and I have sat down
and we thought it through,
and now we know we're right.
Bullshit.
You can't do it.
Well, you know, and again,
sometimes what it wants to
be a collections business
for single moms now you want
it to be right, not only not
what you wanted it to be,
but something you won't
even tolerate it being.
That's what I'm, it's
like, okay, I'm done.
I'm out.
I've seen a lot of cases where
people build a product and
there's some services to help
get the product to go, and after
a while they're like, yeah,
it's kind of just a services
business that kind of has like
a product tchotchke to kind
of get it started and I don't
wanna service the business.
That's okay too.
Meaning that if that's not
the business you want, if
you don't wanna collect from,
uh, payments for Xboxes, for
single moms, don't do it.
Right.
That would've been a great
pitch deck, like intro page.
Right.
Collecting from single moms.
People been throwing
money at you.
Yeah.
Putting the screws
to single moms.
Yeah.
Actually, you know, I. We
had a couple of investors
who, while we were on the
campaign trail raising money
kind of said exactly that.
They were like, Hey, well
at the end of the day, won't
you be collecting from people
that couldn't otherwise make
their payments, et cetera.
Right.
Which is a reasonable question.
And my whole point was, yes,
there are people who need to
buy things that don't have that
amount of money, but we're gonna
do it in payment terms that
they can actually afford, like
on very tiny payments over,
over a, a short period of time.
And that was true,
but that doesn't mean
everybody's gonna pay us.
Right.
And so at the end of the day,
you're still gonna collect from
people that just didn't want
to pay you, whether they could
or not put on your loan shark
suit, start knocking on doors.
Yep.
Exactly.
What it's so part of it for
me, as I've been, you know,
involving myself, has been
taking my ego down a notch.
Yeah.
Being like, I don't
have to be right.
The product has to be right.
I don't have to be Right.
Which is the advice that
you got, and I think part
of it too is detaching
yourself from the product.
Meaning like, if this doesn't
work, it doesn't mean I suck.
It means a product I
built isn't working.
Not the same thing.
Yeah.
I think that that separation
of self is one of the hardest
things to do depending on
where it comes from, right?
Like I think there are times
where like you build something
more opportunistically and
maybe you're not as personally
attached to the outcomes.
I'd argue that's a bad
business to build in the
first place because you're
probably not gonna survive it.
But like I, I think that's.
It's a necessary piece, right?
We have to be able to,
to, to separate ourselves
to a healthy degree.
At least say like, look, I
wanna be involved in this,
but I'm not this, right?
Right.
There's an old farm joke
that talks about involvement
and commitment, the pig,
and it's, uh, it, it
goes to breakfast, right?
It's like the chicken is
involved, the pig is committed.
Committed.
Yeah.
You gotta be the chicken, right?
You gotta be the chicken.
In the startup case.
Within our own company though,
Ryan, one of the things I'm
very proud of that we've
done culturally is while we
all, you know, have a million
opinions, strong opinions on
things of, of what we think
should be right, what the
product should be, et cetera.
I think partially because
we've worked together for
so long and we've seen this,
you know, work so many times,
we're naturally slightly
less committed that way.
In other words, we're like,
like you and I yesterday,
we were talking about, um,
landing pages and, and what the
messaging should be, et cetera.
We both have ideas
of what could work.
Yeah.
But we, we've both done
this enough to know.
Hell we know, right?
Like put it up
for some testing
That's I'm saying market,
like try everything, try
everything and, and, and,
and separate ourselves.
And that's the thing, like
at the end of the day, we've
gotten to a great place where we
want to find out what's right.
I don't care which
one of us is right.
I'm not like, oh, another check
on the, on the wall for me.
What was wrong and I was right.
Like, who cares?
We just want to get to Right.
But that goes back
another couple steps.
That goes back to the point
where we're saying what matters
most to us in this business
and, and it was something
that we fundamentally,
early on we said like, do
we care about crowdfunding?
No.
Do we care about customer
acquisition for startups?
No, not, not really.
Right?
Do we care about any of the
other things that we built?
Not in that sense, but what
we care about is the, is the
outcomes created and for whom
we care about founders, right?
So at the end of the day, like
when, when we can separate all
that and just go, is this gonna
be the best thing for the people
that we're trying to reach?
It's gonna help 'em understand
what we do so that they can
get to value quickly and go
on and do what they wanna do.
This makes it a hell
of a lot easier.
Right.
But that goes back to the
core principle that you talked
about, which is not being
stuck on whatever that first
thing we thought was, and
then trying to force function
that into people's lives,
whether they need it or not.
Disaster.
Another way to be saying like,
like if someone were to say,
Hey, this is, you know, this
business I'm building, it's
going great, et cetera, and
my question would always be.
Compared to what,
what else did you try?
What else have you done
to prove that this is
the best thing for you?
Uh, like, I'll, I'll
give you an example.
When people talk about the
startups.com model, like
what we do, they could
pose the same question.
They could say, well, you
know, aren't there other
things you could be doing
that would make more money?
And my answer is yes, if
that were our only selling
Xboxes to moms, right?
Single moms, right?
Yes.
There's a lot of other things
you could do that would make
more money that we ne don't
necessarily want to do.
C selling Xbox to moms, right?
Yeah.
Like, so it's not always
about, again, uh, the
answer is always what makes
the most money, right?
Sometimes the answer is,
is what makes you happiest,
makes you most satisfied.
We believe the customer, uh,
deserves things like that.
But what's important is
that you're challenging
yourself, right?
That, that you're saying,
Hey, we believe this is the
path, but have we challenged
other paths to confirm
that this is the path?
Because I, I think that's,
I think that's where.
Companies lose their edge
when they say, Hey, this is
the way we've always done it,
so this is the way we do it.
Which is exactly how the
company that's gonna eat your
lunch right, gets introduced.
I always think of companies
like, this is maybe a
bad example, maybe not.
I. Of Intuit.
You know, Intuit's actually
a phenomenal company as far
as its performance, like
the, the fact that it was
able to buy companies like
Credit Karma or, or MailChimp
and things like that.
Yeah, yeah.
Just shows like how
much strength there is.
Yeah.
These weren't small
transactions either.
They
were not small transactions,
but at the same time, here's
a company that still builds
Turbo TurboTax, like it's being
installed on Windows three 11.
Right.
It's not like nobody there is
like, Hey, shouldn't this be
like a super cool like Web3
0.0 style ux or something?
Like, they're like, Nope, nope.
Windows three 11, right?
Yep.
That's 14.
Plop install it.
Right?
They, they still use the
same jokes when it's loading.
I love Turbo.
I, I love the idea of TurboTax.
I use TurboTax, but it is easily
the most outdated piece of shit
software I've ever seen, and.
I can't figure out how that
isn't a call for literally a
million other companies to be
able to dominate that space.
But, but my, but that's my point
here is a product that clearly
has not evolved, uh, which to
me is dying for a competitor.
Yeah.
And yet for whatever reason,
I mean, I guess part of it,
there's just, there, there's,
there's a lot of, a lot of
weight to the incumbency there.
Right.
So that, that's part of it.
But Yeah.
But if they don't change, yeah.
They haven't evolved.
Right.
Yeah.
But if they don't change,
and I think for many of us.
Change is scary.
Uh, change is not only scary
because it's tough for us
because as leadership, you
know, we're taking a gamble
every time we make a change.
It's tough for us to be able to
take the entire organization,
all the people associated
customers, investors, right.
And get all of them to
change and get all of
them on board with that
change because they look at
change being scary as well.
Yeah.
I think in general,
this kind of.
Comes back to the fact
that founders, if, if, if
we're gonna evolve, right?
If we're gonna, if we're
gonna change who we are,
you know, we've gotta
be willing to evolve.
Ryan, I can't think of anybody
that has done really well that
hasn't been willing to kind of
burn it all down at least once
to do it differently, you know?
Yeah, yeah.
No, for sure.
In the startup space,
absolutely not.
It's uh, it's part of it,
I think, you know, but, but
let's, let's stick on that.
The, the burn it all down
and start again thing, right?
Where do you stand on.
Small versus radical
pivots, right?
Like, I feel like this is
in, in the startup space, we
often just see like there's
these wholesale changes and
sometimes that works out.
We hear the stories
where it works, right?
And the ones that, that
where it doesn't work, we,
we don't hear about them
because they just disappear.
But like, I. How can we try
to approach these things
from a minor tweak versus a
total overhaul perspective?
Because to me that's always
significantly easier, right?
Behavioral change,
the fear factors, all
that stuff goes down.
But how often in your, in your
recollection was it sort of,
I. We can do this by making a
bunch of little turns versus
trying to shove the Titanic
all at once past the iceberg.
I think that's a great point.
I think that the, the best
way to start is by showing up
today, tomorrow, and opening
the conversation with your
team about whatever topic
it is, no matter how minor.
Say, Hey, let's level set here.
Uh, step one.
None of us knows the answer.
We all have opinions.
We all have strong opinions on
what we think the answer might
be, but the answer itself,
we can't know until we've
taken action and responded.
So if we're gonna pivot to a
new product, you might have a
strong opinion of why it won't
work, but let's both agree that
neither of us actually knows.
Right.
So we can't argue this or
prevent ourselves from evolving
from a position of certainty.
You can't possibly do that
because blah, blah, blah.
Right?
You can't possibly do that.
And there might be risks,
but it doesn't mean you
can't possibly do that.
And so I think for, for
all of us as founders.
If we're going to evolve,
if, if we're going to be
able to adapt and change the
organization or maybe prevent
ourselves from staying on this
ridiculous path that is not
getting us any further, that's
putting us kind of like out to
pasture as we speak, or it's
not making any money or not
keeping us viable if we can't.
Take our ego off the table.
If we can't get to the point
where we're willing to make
a wholesale change for the
better of the company, even
if it's at the expense of us,
then we're never gonna adapt.
We're never gonna evolve,
and we deserve that fate.
But if we can change that, if
we can change that process,
if we can change that process
ourselves and be open to
making those changes and
evolving the way we need
to, then our business could
be a hundred x what it is
today if we just let it.
Overthinking your startup
because you're going it alone.
You don't have to, and honestly,
you shouldn't because instead,
you can learn directly from
peers who've been in your shoes.
Connect with bootstrap
founders and the advisors
helping them win in the
startups.com community.
Check out the startups.com
community@www.startups.com
to see if it's for you.
Could be just the
thing you need.
I hope to see you inside.